Metal-Free Oxidative Carbon-Heteroatom Bond Formation Through C-H Bond Functionalization

被引:242
作者
Samanta, Rajarshi [1 ]
Matcha, Kiran [1 ]
Antonchick, Andrey P. [1 ]
机构
[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany
关键词
Metal-free reactions; Green chemistry; Reaction mechanisms; Heterocycles; C-H functionalization; Hypervalent iodine; ONE-POT SYNTHESIS; HYPERVALENT IODINE(III) REAGENT; TRANSITION-METAL; HIGHLY EFFICIENT; INTERMOLECULAR AMINATION; N-ACYLAMINOPHTHALIMIDES; RADICAL AZIDONATION; CATALYZED SYNTHESIS; C(SP(3))-H BONDS; PRIMARY ALCOHOLS;
D O I
10.1002/ejoc.201300286
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct methods of carbon-heteroatom bond formation through functionalization of non-reactive C-H bonds represent an attractive approach to the synthesis of interesting products. This review focuses on the development of metal-free coupling methods for unactivated compounds under oxidative reaction conditions. The utility of these methods in syntheses of desired products and the mechanisms of their formation are discussed with numerous examples.
引用
收藏
页码:5769 / 5804
页数:36
相关论文
共 161 条
  • [1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [2] Radical Amination of C(sp3)-H Bonds Using N-Hydroxyphthalimide and Dialkyl Azodicarboxylate
    Amaoka, Yuuki
    Kamijo, Shin
    Hoshikawa, Tamaki
    Inoue, Masayuki
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) : 9959 - 9969
  • [3] [Anonymous], 2012, ANGEW CHEM, V124, P8201
  • [4] [Anonymous], 2008, ANGEW CHEM
  • [5] Antonchick A. P., 2011, ANGEW CHEM, V123, P8764
  • [6] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature
    Antonchick, Andrey P.
    Samanta, Rajarshi
    Kulikov, Katharina
    Lategahn, Jonas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8605 - 8608
  • [7] Synthesis of carbazolones and 3-acetylindoles via oxidative C-N bond formation through PIFA-mediated annulation of 2-aryl enaminones
    Ban, Xu
    Pan, Yan
    Lin, Yingfu
    Wang, Songqing
    Du, Yunfei
    Zhao, Kang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) : 3606 - 3609
  • [8] An azido-hanessian reaction
    Baruah, M
    Bols, M
    [J]. SYNLETT, 2002, (07) : 1111 - 1112
  • [9] A highly efficient catalyst-free protocol for C-H bond activation: sulfamidation of alkyl aromatics and aldehydes
    Borah, Arun Jyoti
    Phukan, Prodeep
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (44) : 5491 - 5493
  • [10] Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate)
    Celik, Murat
    Alp, Cemalettin
    Coskun, Betul
    Gultekin, M. Serdar
    Balci, Metin
    [J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3659 - 3663